HTTYD - Digimon Adventure 01
by SaurusRock625
Summary: Falling deeper into depression, ten year old Hiccup meets a Night Fury in the woods of Berk and is suddenly transported to the Digital World where he meets a strange creature known as a Digimon. What sort of crazy adventures will he go on now? Find out now. Rated T for strong language.
1. Chapter 1

_**I know that I've written a lot of stories that are kind of out there in terms of their categories, but bare with me on this one, okay? There will be several key differences in the chapters for this story that you won't find in the original Digimon episodes, but for the most part, it will follow the storyline of the original Digimon series. The G1 Digimon, you could call them. But now, without further ado, let's do this thing.**_

_***I don't own How To Train Your Dragon, and I don't own Digimon!***_

* * *

_**Dialogue Key**_

* * *

"Gaossmon Digivolve to… GREYMON!"

'_Greymon Digivolve to… METALGREYMON!'_

**"Gaossmon Warp-Digivolve to… ZEKEGREYMON!"**

_**"****His name is Kuwagamon! He's an insectoid Digimon, vicious and ruthless. With teeth like knives and Scissor Hands that can chop through anything!" = Digimon Data Entries**_

* * *

_**Prologue**_

* * *

For what felt like the millionth time that day, ten year old Hiccup Horrendous Haddock the Third sighed as he was busy with his work in the forge. Mostly cleaning up after his slob of a boss, Gobber. Hiccup is a very small boy, even smaller and thinner than most children in his age group. And considering the fact that he was born in viking society, that's pretty scrawny. He has auburn brown hair that parts to his right and is long enough to fall over his eyes which are a dull green color, and pale skin that has a dusting of freckles on it. He's wearing a long green tunic with a bearskin fur vest that matches his boots over it, and a pair of grayish-green pants with laces at the bottom.

As he swept the floor, his depression began to act up again as he could feel the cold and uncaring stares of the villagers as they passed by the stall after picking up their repaired weapons or buying new ones once their old weapons could no longer be used.

They always thanked Gobber for all he did to help them, but whenever he sharpened or repaired someone's weapons, they'd just take them back without giving him any form of thanks. Some even sent hateful glares his way when they thought no one important was looking. Hiccup did his best to ignore them as usual, but it was getting increasingly difficult to do so.

"Ey, 'Iccup. Wha's wrong wit ya, lad? If yew keep sweepin' tha' spot there, it'll be so clean Ah'll see myself in the floor." Gobber asked, having noticed his apprentice's unusually sluggish attitude.

"Oh, uh, it's nothing. Really, I'm just really focused today, Gobber." Hiccup said in response.

Returning to his work and trying not to let his depression be known, the boy went to the grinding wheel and started to sharpen an axe while Gobber looked at his apprentice with a combination of sympathy and suspicion. He knows that Hiccup has been being treated a lot worse than usual and was just trying to cover up that pain he was feeling so that he wouldn't be pestered about it. Quite frankly, Gobber doesn't understand why everyone keeps calling his apprentice 'useless' when he's got more talent in his wee pinky finger than all of them have in their whole bodies.

Heck, Hiccup is the one doing a vast majority of the repairs and enhancements to the village's weapons and defenses, the villagers just don't want to admit it. Not to mention he's the only other viking on this whole island who has any artistic skill.

The only viking of Gobber's generation who has artistic skill is Bucket. Things like drawing and sculpting are not very common skills around Berk, and Gobber knows it's important to pass on the tricks of the trade to each new generation in order to preserve the skills that one acquires in their lives. Since nobody wanted to be Bucket's apprentice due to his own below average intelligence, and that's saying a lot considering most vikings don't even know the meaning of the word 'calibration', both Bucket and Gobber feared that the skill would end on Berk when Bucket dies.

Knowing that his apprentice wouldn't be able to work as quickly or efficiently as he normally does in this state, Gobber sighed and turned to his apprentice.

"Alright, lad, just hang up my spare appendages for my arms and then take the rest of the day off. It's clear ta me that yew need ta take a walk ta clear yer head. And Ah'm not takin' no fer an answer." Gobber ordered.

Hiccup sighed as he knew it would be impossible for him to win an argument against his meathead of a mentor in blacksmithing, he just set out to take care of it and get it over with as quickly as he could. Maybe he'd have some peace and quiet out in the woods away from Berk.

* * *

In the Great Hall where all of the important meeting for the Hairy Hooligan Tribe and sometimes their meals took place, chief Stoick 'the Vast' Haddock was busy going over a few of his duties as Chief. And to a tribe of vikings, that's a lot of jobs. But his mind was not entirely on his work. It kept drifting to his son and the heir to the throne of Chieftain, Hiccup.

So far, there hasn't been so much as one complaint from the villagers, namely a certain cranky old man named Mildew, in regards to the lad and anything he might have done wrong. And that's got him a bit on edge. That normally means that something really bad is about to happen.

The great chief of Berk sighed as he ran a large, beefy hand down his face. His son was just so different from all of the other viking kids at Berk. He has the attention span of a sparrow. He took the kid fishing once, and the boy went out hunting for - for trolls! Stoick can hear Gobber's words now…

Trolls exist! They steal your socks! But only the left ones. What's with that?

Stoick still remembers when he was a boy. Only a couple of years older than Hiccup. His father told him to bang his head against a rock. At the time, Stoick thought it was crazy, but he didn't question his father. And you know what happened? That rock split in two! It showed the man what a viking was capable of. He could level forests! Tame seas! Even as a boy, Stoick knew what he was. What he had to become.

Hiccup is not that boy.

But thinking about it now, Stoick also knows that Hiccup took more after his long since dead wife, Valka.

They both have great artistic skills and were both many things in life. But never have they been dragon killers. It's the exact same reason that Valka ended up taken by that four winged dragon when Hiccup was but a year old. She couldn't kill that devil, and it set the house on fire before flying off with her. And Stoick was left with two things. A broken heart, and a sickly son who he had to raise by himself.

Now, the chief of Berk knows that he hasn't exactly been what most would call a model father. But Hiccup is a viking! He needs to toughen up and build his character. And as the future chief of Berk, Stoick feels as though he needs to be especially tough on the boy to help him become the man he needs to be. It's one of the reasons why he set Hiccup to work in the forge with Gobber as a blacksmith. And yet in addition to learning how to work with metal, it triggered the boy's creative side even more as he tried to make crazy contraptions to help the village.

Unfortunately, those inventions of his usually cause more damage than they're worth. Like that time he tried to create something he called a flamethrower and accidentally set Fungus, Mildew's pet sheep, on fire. Fortunately and yet extremely unfortunately for the poor animal, only the wool was burnt so the sheep was okay after that little incident.

And although Stoick will never admit it, he actually thought that incident was absolutely hilarious. I mean, how many times outside of a dragon raid do you get to see an old man trying to chase a flaming sheep with a bucket of water?

But now, Stoick finds himself facing a new problem. A problem that all of his chieftain training couldn't possibly prepare him for. And that problem is…

...How to be a better father to his son.

* * *

Flying out of the fog that surrounds Dragon Island, a ten year old dragon known as a Night Fury was flying away from the island in search of new lands and freedom. And to hopefully find friends and a family of his own.

It ain't fair.

This little guy is the only one like him he's ever seen, possibly the last of his species, and is often mocked by many of the other dragons in the nest for being so.

If Night Furies are so powerful, then why are there so few of you? That's what they all say. Well, all except for a few dragons who are strong enough to mostly resist the commands of the nest's queen. They all left a couple of days before this Night Fury did, and when they did they urged him to leave with them.

But he was scared.

Scared to leave the only real home he's ever known. Scared of being killed by those two-legs who call themselves humans. But most of all, he was scared of being left behind and being all alone all over again.

But he's finally had enough of living under the rule of a tyrannical queen who will eat her own subjects just because they can't bring her enough food from those humans during their raids. Honestly, they lose more of their numbers to the two-legs than the amount of food they can bring her, and she depletes their numbers further by eating those who bring hardly any food. Mainly the more lazy Gronckles.

So now, this young Night Fury is off for a, hopefully, better life. His destination? Berk.

* * *

_***To Be Continued…***_

* * *

_**Okay, that's all I have for the story right now, but next chapter is when we really get into it. For now, I have a few questions I need you guys to answer, if you don't mind. Ahem!**_

* * *

_**1.) Do you guys want Hiccup to have a standard Digivice like the rest of the Digidestined, or do you guys want him to have a Fusion Loader? (Please say why you chose your choice.)**_

**_2.) Should time in the Digital World and Hiccup's world be synched, or should there be the same time difference between Digi-World and Berk as there is between Digi-World and Earth?_**

_**3.) Do you guys want the rest of the Digidestined to train dragons like Hiccup will? And if so, what dragons do you want them to train?**_

_**4.) And finally, do you want Astrid to become a part of the Digidestined around the same time Tai's sister Kari does?**_

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_**Thanks for giving this story a chance, guys. See you all next time.**_


	2. Chapter 2

_**For a moment, I was worried that no one would like this story, but that fear's been put to rest. Now that the prologue for this story's been taken care of, let's move on to the rest of the story, shall we?**_

_***I still don't own How To Train Your Dragon, and I don't own Digimon!***_

* * *

_**Dialogue Key**_

* * *

"Gaossmon Digivolve to… GREYMON!"

_'Greymon Digivolve to… METALGREYMON!'_

**"Gaossmon Warp-Digivolve to… ZEKEGREYMON!"**

_**"His name is Kuwagamon! He's an insectoid Digimon, vicious and ruthless. With teeth like knives and Scissor Hands that can chop through anything!" = Digimon Data Entries**_

* * *

_**Dragons and a Dragon Rider!**_

* * *

Hiccup kept walking through the dense forest of trees that surround the outskirts of Berk as he tried to find a place to, hopefully, get some peace. But something tells him that so long as he's on this island, he'll never truly be at peace. Especially since he's always beaten up and blamed for stuff he didn't do by his arrogant cousin, Snotlout Jorgenson, and the other village boys from the neighboring tribes. And what has his father ever done to help him?

Nothing! Zip! Nada!

He came home beaten bloody, black, and blue one day, and all Stoick does is tell him that he needs to hang around Snotlout more! He is a terrible father!

Finally, Hiccup reached his intended destination. It was a beautiful cove with a few trees, some rocky croppings here and there, and a shallow lake that had a variety of tasty fish swimming around in the deeper parts. He found this place a couple of months ago when Tuffnut and Ruffnut had chased him into the woods hoping he would get mauled by wild boars or wolves. The kid took shelter in a small cave after finding this place, went home in the morning, and surprisingly, Stoick didn't question where he had been all night.

Walking over to his favorite tree, Hiccup sat down and finally began to release all of his pent up feeling the only way he really knew how at the moment. Crying like the small child he is.

Hiccup was tired of it all. Tired of being viewed as a mistake. Tired of being bullied just because he's not like the other vikings. Tired of being ignored and neglected by his father. And most of all, tired of living on an island full of villagers who would rather see him dead rather than have him as their future chief.

The boy was so distraught and distracted by his crying that he didn't notice something land in the cove and walk over to him. Not until he heard a beastly snort and felt a small blast of steam hit him in the head. Hiccup looked up and saw what many in his village have never seen before but he seems to instinctively know what it is.

A Night Fury… the unholy offspring of lightning and death itself.

The dragon certainly is nothing like the ones Hiccup has ever seen. For one thing, it's smaller than most other dragons even though he can tell that it's not full grown. But it's like no dragon Hiccup has ever seen before. The way its body is structured makes it looks sort of like some species of big cat, like a panther or a mountain lion, and its body is coated in jet black scales that easily help it blend in with the night. It also has these two smaller wings beneath its main wings that are probably meant to help it achieve its famous high speed when it flight, along with two fins on its tail. If Hiccup were to wager a guess, those fins are meant to help with directional control while in flight. It also has these six appendages on its head and green eyes.

Hiccup smiled as he knew that his prayers to the gods have finally been answered. He would finally be free of the suffering that he has always been through at the hands of the villagers. Oh sure, there will always be a couple of people he'll miss when he's gone. People like Gobber, Astrid, and even Fishlegs. Maybe even the twins to a degree. When they pranked him, they did it just to get a laugh, not with the intent to hurt or make him miserable.

But he certainly won't miss Snotlout, who took advantage of Ruff and Tuff's low intellect to basically turn them into his henchmen.

Hiccup abruptly stood up, grabbed his dagger from his belt which, he noticed, made the dragon tense, and threw it into the deepest part of the lake where he knew he'd never be able to retrieve it. He then faced the dragon and spread his arms out side to show that he was completely defenseless.

"Well, go on and get it over with, dragon! Kill me and avenge all of your dragon brothers and sisters who have fallen to the blades of my kind!" exclaimed Hiccup.

The Night Fury just tilted his head curiously, much like a cat would. Why would this human boy want to be killed by him? Does he think he's here to do so? Does the human think that dragons eat humans? No thanks! The Night Fury would honestly prefer fish or a nice big slab of beef instead of human meat. Besides, even if he WAS going to eat this human, the little guy's too skinny. And that's not good. He really needs to eat more.

Especially if he's going to eat Icelandic Cod. Those are especially delicious.

Now he's hungry.

"WELL!? WHAT'RE YOU WAITING FOR, HUH!?" Hiccup snapped at the Night Fury. "I'M UNARMED! A PERFECT TARGET FOR YOU! SO WHY DON'T YOU JUST GO AHEAD AND KILL ME ALREADY, YOU USELESS REPTILE! DO IT! I'M THE CHIEF'S SON! THE ONLY CHILD OF THE MAN WHO HAS SLAUGHTERED BILLIONS OF YOUR KIN! SO HURRY IT UP! GO ON! JUST… please… kill me…! End my miserable existence now…!"

No longer having the energy to show any form of anger, Hiccup just collapsed to his knees as tears freely fell down his face. The Night Fury was beside himself with worry. He's never heard any creature sound so broken before, and it scares him. This human child can't be any older than he is, even though he's clearly smaller than he should be and way underfed.

What has this child suffered at the hands of the monsters who dare call themselves his parents!? The Night Fury had to do something to save this boy from his depression. But what could he do? Being in the presence of this human child certainly made him realize something important.

They really are a lot alike. They were both alone in the world. They didn't fit in with their respective tribes, they harbored feelings of great destruction and they both seemed to be somewhat emotionally damaged. So, thinking back to his time as a hatchling, the Night Fury walked up to the boy and did something that his Egg Mother used to do for him.

He got up on his hind legs, walked over to the crying child, and wrapped his forelegs and wings around the boy, bringing him into a hug.

When Hiccup heard the Night Fury walking closer to him, he internally celebrated. Maybe the dragon had actually been paying attention and was going to finally end his misery. But rather than outright kill him or even eat him, the dragon did something that surprised Hiccup greatly.

It hugged him.

Hiccup couldn't even remember the last time he's been hugged by anyone in his life. Not since his mother, Valka, was killed by a dragon during a raid when he was a baby.

He felt something wet falling on top of his head and looked up to see that there were tears falling from the eyes of the Night Fury. Sorrow was present in the dragon's eyes, and that sorrow was directed towards… Hiccup?

Why though? Why would a Night Fury, the unholy offspring of lightning and death itself, cry over someone as worthless and useless as Hiccup (thinks he) is. The dragon sadly cooed as he hoped that showing Hiccup some much needed kindness might help to ease the pain.

Fully realizing now that the dragon was sad for him, Hiccup did the one thing he never thought he'd do in his life. He hugged the dragon back.

He felt happy. Happy that someone cared enough about him to actually try and comfort him in his time of sorrow. Even if it was his sworn enemy.

_'No,'_ he thought. _'Not my enemy. Berk and every other viking in that wretched village are enemies to dragons. But I'm not one of them. And I never will be!'_

Looking up at the Night Fury, Hiccup managed a true smile through his still teary eyes. A smile that the dragon found fascinating and tried to mimic, showing to Hiccup that there were gums in his mouth rather than teeth.

Hiccup didn't understand why this dragon doesn't have teeth when he clearly had them during the beginning of his emotional rant, but right now, he doesn't care. He felt safe and content in the wings of his friend.

The boy yawned as the emotional and physical exhaustion began to take its toll.

"Thank you for being there… Toothless." Hiccup yawned before drifting off to sleep.

The dragon felt confused by what this boy had just called him. Toothless? Was that supposed to be a name the boy wanted to call him? If it was, he found himself liking it, strangely enough. Toothless the Night Fury. A perfect name for a mighty creature of the night such as he.

Toothless yawned as he too was beginning to get tired. He used up a lot of energy during his flight to the island from that accursed nest and needed to rest and regain his lost power. So, being mindful of his new friend, Toothless settled down on the soft grass of the cove and went to sleep. Thoughts of adventure and flight taking hold in his mind.

Oh, if only he knew just how right he was about there being adventure in his and Hiccup's future.

* * *

In another part of the world, another dragon is also flying towards Berk in search of its purpose in life. Or rather her purpose. That's right, this dragon is a female. And she actually looks mostly the same as Toothless, but with a lot of key differences.

She is shown to have blue eyes and white scales with glittering textures. She has a single, long spine running down her back rather than individual curved spines, a pair of big ear-like adapters on the top of her head, and two smaller ones on the side. She also has triangular wing flukes and tail flukes that are glittery white in coloration. Her wings are glittery white with glittery pink stripes running down her wings.

The Viking's don't know it yet, but this dragon is what's known as a Light Fury. A brighter and even more reclusive subspecies of the Night Fury family tree. And she is on a mission of great importance. One that she has given to herself.

Her parents always told her of a world beyond their own. A world of bipedal ape-like creatures known as humans. Her father and mother told her that while this world is beautiful, it is also a dangerous one where dragons and humans are at constant war with one another and that she must never go there.

But it got her to thinking: are all humans bad?

Surely not all of them are dragon killers like her parents told her. After all, she knows from personal experience that there are good dragons and there are bad dragons. So why can't the same principle apply to humans? And so, she made her most daring move she's ever made in her young life.

She left the safety of the Hidden World to go human hunting.

Now, please don't misunderstand. She doesn't intend to harm any humans. She wants to find that one ideal human who will be her partner and friend. Someone who will watch her back just as she would theirs. And she has a feeling that the human she's looking for is somewhere in this direction.

Let's just be glad that Berk isn't in the middle of a raid right now so she can easily infiltrate the surrounding area to find her rider.

* * *

_***To Be Continued…***_

* * *

_**Okay, so as you all have just seen, I've decided to include the Light Fury in this story and she will have a human partner. You'll find out who in the next one. But now for the questions.**_

* * *

_**1.) I've decided that Astrid will be a Digidestined. What Digimon do you guys want her to have as her partner and why?**_

_**2.) What kind of Digivice should I give Hiccup and Astrid? (G1 Digivice, D-ARK, Data Squad, Fusion Loaders, etcetera)**_

_**3.) What dragons do you want Tai and the others to train? (Please be specific. Give species name, gender, and color ideas if you have any.)**_

_**4.) And finally, would you guys like me to do a Watching series for this story? (Not sure how well I'll do, but I'll try.)**_

* * *

_**Thanks a bunch for watching, and I'll see you all next chapter. Adios!**_


End file.
